Carbon tetrabromide → 1,1'-Biphenyl, 4-(3-bromopropoxy)-

Participants

Reaction Steps

To a solution of 3-(biphenyl-4-yloxy)-propan-1-ol (1.00 g, 4.38 mmol) in CH2Cl2 (20 mL) at 0° C. was added triphenylphosphine (1.61 g, 6.14 mmol) and carbon tetrabromide (1.81 g, 5.47 mmol). The reaction mixture was allowed to warm to room temperature, stirred for 1 hour, and extracted with ethyl acetate (50 mL). The organic layer was washed with H2O (3×50 mL) and bine (3×25 mL), dried (MgSO4), filtered and concentrated. The crude product was purified by silica gel column chromatography (silica gel, hexanes/ethyl acetate, 9:1) to produce 4-(3-bromo-propoxy)-biphenyl (1.22 g, 95%). 1H-NMR (200.15 MHz, CDCl3): δ 7.57–7.29 (m, 7H), 6.98 (dd, 2H, J=6.72, 1.88), 4.15 (t, 2H, J=5.92), 3.62 (t, 2H, J=6.44), 2.34 (qn, 2H, J=5.92).

Provenance & Evidence